This blog is 20 years old. I started with static files generated from CityDesk and hosted on a simple server. Then, I went to static files generated from RapidWeaver on Mac. In 2012, I realized that I needed it to be easier to post, so I migrated to WordPress.
I very rarely updated this site in 2012. I finally decided to bite the bullet and get everything into WordPress so that I could update from any machine, not just the one I had RapidWeaver installed on. I immediately got a bunch of benefits (1) the site has a mobile theme (2) I can update from my phone or iPad using WordPress apps (3) dealing with images and other media is a lot easier and (4) publishing is automatic and fast. Since the migration, I have maintained about a weekly update schedule.
I have been on WordPress since then and can’t see any reason to change. A few years ago, I migrated to DreamHost, which I recommend for WordPress hosting. They can do more than WordPress—I also host App-o-Mat there (which is a custom Django site).
My theme is WordPress’s Twenty Twelve. Each year they make a new theme (named for the year). It was the default when I migrated, and I didn’t look for anything else because I wanted something plain, which it is.
I really try to limit my plugins. There are three that I recommend if you need the features they implement.
I use the Blubrry plugin to help me self-host my podcast. It generates the podcast feed automatically from blog posts.
I use the Contextual Related Posts plugin to put related links at the bottom of each post and the Exclude Pages from Navigation plugin to let me control which pages show up in the navigation.
Aside from those, I just picked the most popular ones for generating a sitemap and to make it easier to embed videos hosted on YouTube and Vimeo.
I use Hover as my domain name registrar.
I have no plans to change anything. I do keep an eye on the CMS sites that offer some distribution (Medium, Substack, etc), but I care too much about owning my URLs and keeping content in something I could easily migrate away from.